Top Condo Rentals in Osceola County in 2026

Osceola County Condo Rentals
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Our top choices for Osceola County condo rentals

Lifetime of Vacations Resort

3.0 star property

Kissimmee

9.4 out of 10, Exceptional, (176 reviews)

9.4/10

Exceptional

(176 reviews)

"We love coming here when we visit Orlando. The rooms are amazing and perfect for our needs. The beds are comfortable too!"

Alena

The price is HK$517

HK$517

HK$720 total

includes taxes & fees

2 Aug - 3 Aug

Lifetime of Vacations Resort

Disney Escape | Renovated Windsor Hills Condo w/ Balcony & Themed Bedrooms

Windsor Hills

9.8 out of 10, Exceptional, (31 reviews)

9.8/10

Exceptional

(31 reviews)

"Love it, will stay again for family vacation "

Maikor V.

Disney Escape | Renovated Windsor Hills Condo w/ Balcony & Themed Bedrooms

1st Floor • Free Parking • No Resort Fees • 14 minutes to Disney • 5 min shops

Kissimmee

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"We were pleased to stay at this place. We liked that it was located on a gated community and that it was relatively close to Disney's parks."

Luisa G.

The price is HK$720

HK$720

HK$974 total

includes taxes & fees

25 Aug - 26 Aug

1st Floor • Free Parking • No Resort Fees • 14 minutes to Disney • 5 min shops

Lakeside-Beautiful 3 bed Oakwater condo over the lake, just 1.5 miles from WDW!

Kissimmee

9.4 out of 10, Exceptional, (129 reviews)

9.4/10

Exceptional

(129 reviews)

"Nice place, we really enjoy our stay Great location!"

Patricio V.

Lakeside-Beautiful 3 bed Oakwater condo over the lake, just 1.5 miles from WDW!

Dream Disney Family Vacation, Best Resort, 2 Miles To Disney, Space For 8

Windsor Hills

9.2 out of 10, Wonderful, (160 reviews)

9.2/10

Wonderful

(160 reviews)

"This place was perfect for our family of 6 stay. The water slides are so fun for the kids and it’s close to Disney! Very clean property."

Kristy P.

Dream Disney Family Vacation, Best Resort, 2 Miles To Disney, Space For 8

SUNNY DISNEY ESCAPE: as close to Disney as you can get with the comforts of home

Windsor Hills

10.0 out of 10, Exceptional, (165 reviews)

10/10

Exceptional

(165 reviews)

"Ann was extremely welcoming and responsive. Condo is immaculately clean and stocked with all the kitchen items and linens you need for your stay. Location is perfect—close to all the amenities. Loved the layout and the black-out shades. Would love to stay here again! "

Anonymous traveller

SUNNY DISNEY ESCAPE: as close to Disney as you can get with the comforts of home

4 bedrooms, memory-foam beds, desk, iron/ironing board

Smart TV, DVD player, books, video library

Coffee/tea maker, fridge, microwave, oven

ON SALE! 4BD 3BTH 1.5 MILES TO DISNEY!

Kissimmee

9.6 out of 10, Exceptional, (129 reviews)

9.6/10

Exceptional

(129 reviews)

"Being this was our family 1st time staying in a house it was good. Very roomy and near by to a lot of food and stores. "

Stanford S.

The price is HK$1,200

HK$1,200

HK$3,288 total

includes taxes & fees

5 Aug - 6 Aug

ON SALE! 4BD 3BTH 1.5 MILES TO DISNEY!

3 bedrooms, iron/ironing board, travel cot, free WiFi

Remodeled~ Themed~Arcade~Windsor Hills~2.5 Miles from Disney World Entrance

Windsor Hills

9.8 out of 10, Exceptional, (197 reviews)

9.8/10

Exceptional

(197 reviews)

"Great location for Disney theme parks and plenty of things to do on property and in the VRBO on days off."

Scott R.

Remodeled~ Themed~Arcade~Windsor Hills~2.5 Miles from Disney World Entrance

Outdoor pool, pool umbrellas, pool loungers

Coffee/tea maker, full-sized fridge, microwave, toaster

40-inch flat-screen TV with cable channels

Magic Tree Resort by Coolvacay

3.0 star property

Kissimmee

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Great hotel friendly staff definitely would recommend"

Tristen

Magic Tree Resort by Coolvacay

Mickey Mouse Farmhouse-Fully Upgraded Condo in Windsor Hills. 2 Miles to Disney!

Windsor Hills

9.8 out of 10, Exceptional, (137 reviews)

9.8/10

Exceptional

(137 reviews)

"We had a wonderful time here and will be back ! The distance to the pool and included amenities for our kids were perfect! Short drive to all the Disney fun, and a couple minutes down the road to Walmart, we are telling everyone about our trip and how we can’t wait to come back! Host was responsive and checking in/out was a breeze. We wish we could have stayed longer!"

Fallyn D.

Mickey Mouse Farmhouse-Fully Upgraded Condo in Windsor Hills. 2 Miles to Disney!

GREAT PRICE! TOP RESORT! On Disney's Doorstep!

Kissimmee

9.8 out of 10, Exceptional, (285 reviews)

9.8/10

Exceptional

(285 reviews)

"It was a nice roomy condo. "

Diana T.

GREAT PRICE! TOP RESORT! On Disney's Doorstep!

Luxe King Suite Bliss Getaway Condo Near Disney

Kissimmee

9.0 out of 10, Wonderful, (42 reviews)

9.0/10

Wonderful

(42 reviews)

"Everything was great! Pictures are accurate and I had a great vacation! "

mike w.

The price is HK$508

HK$508

HK$1,348 total

includes taxes & fees

2 Aug - 3 Aug

Luxe King Suite Bliss Getaway Condo Near Disney

5 Star Resort minutes from Disney 3 bedrooms & 2 baths, Wi-Fi, Pool, Tennis

Kissimmee

9.4 out of 10, Exceptional, (93 reviews)

9.4/10

Exceptional

(93 reviews)

"Loved everything about this condo. Very clean, quiet, and 1st floor, can't get much better. We'll definitely stay again"

Philip J.

5 Star Resort minutes from Disney 3 bedrooms & 2 baths, Wi-Fi, Pool, Tennis

New Water Park! Huge Pool, 5 Minutes to Disney World!🏝

Windsor Hills

9.8 out of 10, Exceptional, (296 reviews)

9.8/10

Exceptional

(296 reviews)

"Condo was great and had everything we needed for a great vacation. Kids loved pool and slides, distance to parks was great!"

Laura K.

New Water Park! Huge Pool, 5 Minutes to Disney World!🏝

NEW LISTING! Wish · Relax · Repeat: 3BR resort condo on Disney's Doorstep

Kissimmee

8.8 out of 10, Excellent, (10 reviews)

8.8/10

Excellent

(10 reviews)

NEW LISTING! Wish · Relax · Repeat: 3BR resort condo on Disney's Doorstep

Be our Guest - 3 bedroom, sleeps 7 + Condo w/ pool view by Disney and Universal

Windsor Hills

9.8 out of 10, Exceptional, (106 reviews)

9.8/10

Exceptional

(106 reviews)

"Our family loved our stay!! The property was very clean and accommodating, had everything we needed. The kids really enjoyed the clubhouse and pool. Great communication with our host, she always answered us promptly with any questions we had. We would definitely recommend this condo and hope to stay here again in the future."

valicia l.

Be our Guest - 3 bedroom, sleeps 7 + Condo w/ pool view by Disney and Universal

Disney Wonder-Beautiful 2 bed Windsor Hills condo, just 1.5 miles from WDW!

Windsor Hills

8.8 out of 10, Excellent, (95 reviews)

8.8/10

Excellent

(95 reviews)

Disney Wonder-Beautiful 2 bed Windsor Hills condo, just 1.5 miles from WDW!

Newly Renovated, Modern Two Bedroom Condo Minutes Away From Disney

Kissimmee

9.6 out of 10, Exceptional, (136 reviews)

9.6/10

Exceptional

(136 reviews)

"Great place! Will stay again :)"

Kristi T.

Newly Renovated, Modern Two Bedroom Condo Minutes Away From Disney

Beautiful Storey Lake condo with views of the lake

Kissimmee

9.4 out of 10, Exceptional, (48 reviews)

9.4/10

Exceptional

(48 reviews)

"Everything was just perfect. Our third stay at Story Lake Resort. This unit was by far the nicest one we’ve stayed in.we intend to rent it again for next year, this time for 3 weeks in March if the price is reasonable."

Gary S.

Beautiful Storey Lake condo with views of the lake

Mickey's Retreat, 3 bed 1st floor Windsor Hills condo-Sleeps 8! 1.5 miles to WDW

Windsor Hills

9.0 out of 10, Wonderful, (43 reviews)

9.0/10

Wonderful

(43 reviews)

"lovely condo, convenient location, very clean. Other than the condo not having any potholders for the kitchen, we had everything we needed. Hosts were responsive to communication. We enjoyed our stay and would definitely stay again!"

Kara J.

Mickey's Retreat, 3 bed 1st floor Windsor Hills condo-Sleeps 8! 1.5 miles to WDW

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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